Choice Series 09: Crossroad Blues
by shadowglove
Summary: Sequel to Family Matters. When the Crossroads Department start having problems with their best agent, Chloe is sent to his specific crossroad to reprimand the agent. Of course she has no idea that he's her ex Groom, Sam Winchester.


**Disclaimer: Don't own Smallville/Supernatural**

Sequel to: Family Matters

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"No, no, you _can't_ just 'pop' in to see him, he isn't the President of the United States or something trivial like that, you need to make a prior appointment with me for a future date." Chloe shook her head as she walked down the darkened streets, phone to her ear. "He's the Father of Darkness. If you can't understand the sort of respect that means he's entitled to then you have no business going to see him to begin with." She pulled a blonde strand behind her ear. "Frankly, I couldn't care less how many legions you captained in hell or how many people's teeth you have fetishly stashed away in whatever pit you call home sweet home. And believe me, Father will be less impressed. _He_ is the one who put you to govern whatever it is you feel you need to boast about, and I assure you, he can easily take it all away and throw you into one of the Pits so you can remember who exactly the boss is around here." Her lips curled in an evil smile as she listened to the response. "I thought you'd see things our way." She reached into her bag and searched around, pulling out her electronic appointment keeper, going over the schedule. "Well, he's booked all throughout this month, but we can pencil you in the first week of next month. How's the third at midday?" She entered the data. "Great. We will see you then."

She put away her devices and smiled as she came to stand before a coffee shop.

Her caffeine addiction was one of the things she had never been able to forget about her human days, and on her worst of nights she found coffee her only savior. The blonde entered the coffee shop and ordered and paid for her drink, emerging from the shop while sipping the delicacy, smiling even as her phone began to ring once more.

Being the personal assistant of the Lord of Evil was a very busy, full-time job...but with coffee all things were possible.

"Chloe Sullivan speaking." She took another sip as she listened to the voice on the other end. "No, I hadn't heard this one. Mel Gibson. Really?" She smirked. "That whole scandal makes _so much_ more sense now." She chuckled. "I think its brilliant." She continued walking down the street. "An extension? We don't give extensions, you know that." The blonde tilted her head. "What could he possibly have to offer? We own his _soul_." With a shake of her head she stopped at a bus stop. "Well you tell whoever this Crossroads is that unless someone else comes and makes a deal on his behalf then there's no extension. He made a deal, and we kept up our end of the bargain, now he has to keep up his." The young female shook her head. "This is common knowledge, how could an operating Crossroads have questions about this?" She pursed her lips. "Well if he was the best Crossroads your department has had in centuries _why_ is he all of a sudden giving you trouble? Have you spoken to Crowley? The Crossroads _is_ his gig." She shook her head. "Right, I'll see what I can do."

Hanging up, Chloe took a long sip of her coffee, shaking her head. "If I don't do it nothing gets done around here." She leaned against probably the only tree in the city, and leisurely sipped her coffee under the flickering street light above. "How did they run things before Manny tricked me into an eternity of this?" Her fingers moved over her phone's keyboard, texting, pressing send before sliding her phone into her bag, concentrating on the nectar of life in her hands.

"You _texted _luv?"

Tilted her head to the side, Chloe took another sip before smirking. "Hello Crowley. Thank you for being so quick."

"Believe me, pet, I've learnt not to cross you." The King of the Crossroads snorted, obviously remembering that day so long ago when he'd made the fatal mistake of teleporting into her Amityville home, leaving the place filled with the stench of sulfur. "So what was so urgent you resorted to _texting_?"

She finished her coffee and dumped the empty cup into a trash can. "Ginny from your personnel department called me in a tizzy over the Mel Gibson deal."

"Ah yes." Crowley grinned. "Closed that one myself."

"Good kisser?" Chloe asked curiously.

"What sort of gentleman do you take me for?" Crowley brought his hand to his chest in mock affront. "When have I ever kissed and told?"

"When _haven't_ you?" Chloe countered.

Crowley eyed her before breaking out into a large grin, chuckling. "True, true. You know me too well."

"You have the best kiss stories," she shrugged, amused. "I like having inside knowledge on who in hollywood or politics or whatever are good kissers." She chuckled. "That's the perk of being the King of the Crossroads, isn't it? Being able to commandeer a client from one of the girls or boys so you can enjoy yourself."

"You make me sound so willful." Crowley tutted.

Chloe raised an eyebrow.

"Once again, you know me so well." The older demon chuckled. "Now, tell me what exactly Ginny bothered you about this time."

"Apparently Mel wants an extension on his deal and instead of telling him flatout that no matter the offer we don't renegotiate, the Crossroads in charge has told him he'd talk to his superior about it." Chloe frowned. "And according to Ginny, this isn't the first time your guy has done something like this. She says that he used to be the best one you have, but these last couple of days he's been missing appointments or scaring clients away with his shitty attitude, or doing crap like this. We can't have Crossroads pulling that sort of shit, Crowley. Damnation is a very busy business, the Crossroads is a big department in it, and we can't have someone bringing down the quality of the work the Crossroads Department has produced ever since you were put in management."

Crowley nodded, smile having melted off of his face as he listened.

"As you know, Father is..._revamping_ a lot of our business, making Damnation seem like a whole new business." Chloe put it as diplomatically as possible. "He hasn't been pleased with a lot that he's been finding. He's already uprooted most of the Elders, and some departments of Damnation are on the chopping block. I don't want to see Crossroads next to them. To be honest, I like you Crowley. You're snarky and flirty and do a damned good job, and I will admit that I have a fondness for the Crossroads Department. It's one of our oldest departments and it would be a shame to see it closed down."

The King of the Crossroads paused for a moment, obviously thinking of how to word this. "Father has caused quite a stir with the changes he's been making."

"That's because everyone's been used to chaos and disorder during his imprisonment." Chloe defended, voice harsh, eyes narrowed. "It was good he returned so he can bring about some order and maybe then we will have a chance in this damned war."

"You're very loyal for a newling, luv." Crowley remarked slyly. "You wouldn't be trying to exchange one brother for another, would you?"

Chloe felt her heckles rose, because although she knew that Crowley hadn't meant it in a bad way others had. Ever since Dean had shocked the Damned by making her, a Newling, his right hand, she'd heard the whispers. Demons and monsters all believed that she was trying to get her claws into the Prince of Darkness, and considering she was fertile, they all assumed that their Dark Lord was claiming her as his so his own bloodline could continue. This line of thought had been strengthened by Dean's announcement that she and her future wouldn't be decided by anyone but herself or him.

"Put away your claws, kitty." Crowley declared, getting all his answers he needed from her body language. "And I think concerning our mutual problem, that you might be able to solve it better than I could." He paused, eyeing her oddly. "This particular Crossroads agent is...special...and I know that I wouldn't be able to get through to him. But your silver tongue and barbed words just might."

Chloe sighed. "I'm not getting home tonight again."

Crowley eyed her curiously. "You've been shouldering a lot of Father's burdens, doll, you're getting wrinkles."

She brought a hand to her forehead and sighed. "My job is to take care of these things so that Father can concentrate on what truly needs his attention...not just these details." The blonde ran a hand over her hair. "Give me the address of this agent's crossroad and I'll deal with him myself."

Crowley's expression was suspiciously amused as he told her the address before disappearing in the blink of an eye.

Raising an eyebrow at the place where the King of the Crossroads had been seconds ago, Chloe took in a deep breath and teleported away to the directions given, finding herself in the middle of the crossroad. Her phone rang right as she was about to call out for the agent to show himself, and she groaned as she searched inside her bag for her phone, finally finding it and raising an eyebrow at the caller I.D. before bringing the phone to her ear. "What do you need?"

"You know, that hurts." Dean sounded far from hurt. "Couldn't I be calling you because I care?"

Her lips twitched. "Dean Winchester, was that a declaration of your love?"

He snorted. "Don't bet on it."

She laughed, shaking her head. "So what _did_ you want?"

"Food. Chinese. From China."

She snorted. "I'm still running some errands, but once I'm done I'll get the food and head straight to your apartment."

"You know, I quite enjoy this at my beck and call thing." Dean admitted devilishly before declaring: "And bring some pie too!" He then hung up.

"Chinese and pie?" Chloe mumbled to herself, shaking her head, stomach a little queasy at the thought of that mixture. "His stomach alone should have tipped his family off to the fact that he wasn't human."

"And here I thought you and Dean were always so uncomfortable with each other." A terribly familiar voice growled behind her. "Yet midnight visits seem normal for you."

Eyes wide, Chloe couldn't control the crazy beating of her heart as she turned around, a gasp escaping her lips as she gazed upon Sam Winchester...and his red eyes.

She couldn't believe what she was seeing, couldn't comprehend how this had happened, couldn't understand why.

Sam was the agent the Crossroads Department was having trouble with...their once star negotiator.

_Sam_.

It was inconceivable.

There must be a mistake somewhere!

"Chloe Ann Sullivan is speechless. Hurry, someone inform the press." Sam's sneer was ugly as he stepped out of the shadows he'd blended in with.

She kept from flinching, understanding his anger towards her. The letter she'd left to break up with him had been purposely cruel and hurtful, and she'd wanted to make him hate her. She obviously had accomplished her goal, and so she hid behind a protective wall in her heart as she forced her face to relax from the look of utter horror she knew she'd given him. "So..." the blonde cleared her throat, raising an eyebrow. "This is an interesting development. Somehow I must have missed your little inauguration."

He was silent was he watched her, fury and anger and so much darkness radiating from him.

"I have to admit I'm curious, last time I saw you...well..." She left that sentence where it stood, tilting her head slightly. "So, how did Azazel manage to twist your arm?"

"As if you really care." He sneered.

Chloe really didn't know how to proceed from here.

If he'd been human she'd have stuck to the bitch card, and yet he was transitioning now, and that meant that he was becoming a demon...would be eternally in her circle...especially since her circle mostly consisted of his brother and father.

Her watch beeped, and she looked down at it, flinching, realizing she was going to be late for that meeting with Alastair. "You know what, I don't have time for this." She gazed back up at him. "It doesn't matter _what_ made you choose this, what matters is you chose it, and since you did you have no right to be slacking off on your job. Especially not the Crossroads. According to your supervisor you're missing appointments and pissing off clients and failing at shit rookies would excel at. I came here to tell the demon in charge of this crossroad to either get his head out of his ass or get out...but considering it's you I realize things are trickier." She ran her hand over her hair in frustration. "Dammit, Azazel never told me anything about you transitioning. He should have given me the heads up."

Her agitation was growing, as was her confusion.

Who else had known about Sam transitioning into demonhood and why hadn't anyone told her about it?

He'd been her Groom dammit!

She'd left him because she thought he wanted to stay human! She'd left so she wouldn't end up sucking the life out of him and killing him!

She _deserved_ a heads up!

And did Dean know?

Her eyes widened, suddenly remembering Dean's words about waiting until Sam had finished his 'training' to tell him about his being Lucifer.

She'd thought Sam had gotten a temp job at a law firm or something! Never in a million years had the thought that Sam was training his demonhood crossed her mind!

"So you had no idea I was transitioning." Sam nearly asked, eyeing her intently.

"Do I _look_ as if I knew?" She snapped, transferring her nervous frustration and anger at his father to him and this situation.

He tilted his head to the side. "Must be a surprise to find out that Dean isn't the only Winchester who's a demon."

Chloe's eyes widened in shock. "You know about Dean?"

But Dean had said he was keeping it secret for now!

"I saw you two together the other day and figured everything out." Sam's smile was ugly as he came towards her, invading her personal space as he sneered down at her. "I always had my suspicions that Azazel was Dean's father as well so it wasn't much of a surprise." He reached out and curled his finger through a lock of her hair. "So how did Daddy Dearest convince Dean of all people to give into his Demon blood? Did he offer him you?" That sneer was terrible. "Did _you_ offer yourself?"

Chloe looked up at Sam, a little disoriented by having him so close to her, actually touching her, to get at first what he was saying. And then his words hit, and it was like a bucket of icy water thrown at her. Her eyes narrowed her eyes and tried to pull away but he tightened his grip on her hair, forcing her to remain where she was.

Sam obviously didn't know as much as he thought he did, because he thought Dean was just a mere demon, not the Prince of Darkness, and apparently believed she'd transferred the Groomship to his brother.

Chloe was getting sick of people thinking that.

She was her own demon for fuckssake!

Eyes narrowed, Chloe tilted her chin up defiantly. "And what if I did?"

Darkness entered those red eyes and before she could even guess what was going through his mind Sam had grabbed her shoulders and lifted her, twirling them around to slam her hard against a light post, causing all the air to escape her lungs in a harsh gasp. He tightened his grip on her, snarling. "How easy it was for you to trade brothers, Bride."

Something inside of her somersaulted at the ease of her rightful title slipping off his lips, but she stomped it down viciously. "What are you playing, exactly, Sam?"

He raised an eyebrow, silently prompting her to go on.

"You didn't choose to be a demon before, we both know it isn't what you _really_ want." She mocked his raised eyebrow. "You love being human, want your life to be an episode of the Brady Bunch or some other annoying All American television show." She sneered, leaning forwards. "Let's face it, you're not exactly demon material."

"Not like Dean?" He growled, looking so dangerous now the demoness should have known better than to push him.

But she'd never been one to play things safely.

"Exactly." She smiled ugly at him. "Now _Dean_ is a demon."

Sam didn't give her a hint, a forewarning, instead forcing himself against her, his lips on hers, every movement punishing and claiming.

For a moment it shocked her, shook her, and she was caught up in it, in the feeling that reminded her of the best years of her life...

...and then she managed to pull out of it and tried fighting, tried asserting her dominance. As an older demon she should be stronger than Sam, should be able to overpower him, and yet she couldn't move an inch. It was almost as if she were trying to struggle against a demon of Azazel's caliber, and that shocked her as she realized that once he transitioned fully Sam was going to be a demon to be reckoned with. That in itself was an aphrodisiac, and Chloe felt her resistance slipping once more despite her mind screaming that things were too confusing and she needed answers, needed _something_!

A whimper escaped her lips as the hands that'd been trying to push away now closed around his shirt, and she allowed him to tilt her head back so as to give him better access to her lips. Her mind and thoughts were slowly fading into a delicious buzz and she didn't even notice their transfer until suddenly she was being lowered onto the soft grass at the side of one side of the crossroads, the grass cool beneath her, Sam's body scalding hot above as he draped himself over her, never once breaking their kiss. One of his hands lowered between their bodies and tugged up the dress she'd been wearing, fingers trailing down to her moist heat. His snarl echoed in her mouth at his disapproval yet arousal at finding her without underwear, and Sam pushed in two large, calloused fingers.

Chloe's body arched as she cried into his mouth, holding on tightly to his shirt. It'd been so long since...she hadn't...not since Sam...hadn't been able to find the desire to...

His fingers seemed impossibly large against her tightness as he curled and plunged them as deep as he could, and Chloe both feared and desired the feeling of something longer, warmer, thicker inside of her.

Suddenly Sam was yanked from her, thrown far away.

Chloe lay on the grass, breathing in and out, confused, disoriented.

"Crowley's been a naughty boy." Lilith mumbled, wearing a cute ten year old, as she bent down and looped her arms around Chloe, pulling her to her feet. "He's going to be hearing from me about this you can be assured of that."

Chloe brought a hand to her head, shaking it, trying to dispel the fog that'd taken residence.

Sam snarled as he returned, eyes redder than Chloe had ever seen on a Crossroads. "What the _fuck_ do you-?"

Lilith raised her hand, adorned by a Hello Kitty ring, white light twirling menacingly. "Really, Sam, you have to get a hold of yourself. You don't even have being an Incubus or something for an excuse. You're being _sloppy_."

He sneered at her. "I don't need some _kid_-."

Lilith's eyes bled white. "I'm _a million_ times stronger than you boy, don't push me."

Chloe turned to Lilith. "What are you doing here?"

"Father needs you, so I was supposed to come and relieve you of your chores so you could go to him." Lilith replied, making a face at Sam. "Good thing I did too, or this one would have caused _war_."

"War?" Chloe squeaked, confused.

"Father might have said that you can't be forced to take a Groom, but you know you're still the demonic version of the Face that launched a Thousand Ships." Lilith smirked. "If word had gotten around that the first person you had lain with after leaving Sam Winchester was in fact Sam Winchester...things would not be pretty." She made her face. "I know my brother also would not be happy, and he has more than enough power necessary to destroy a demon not fully transitioned."

Given his newly obtained bad attitude, Chloe would have expected Sam to be cursing and snarling and doing something very disagreeable, but instead the red had faded out of his widened eyes and his lips had parted in shock.

She sent him a confused look, tugging down on the hem of her dress self-consciously, turning her attention back on Lilith. "Why exactly would Belial do this?"

Lilith snorted in amusement. "Not just Belial, honey. Ever since you and this one's engagement got broken off Open Season on the position of your Groom has been going on. Why do you think you've gotten less and less offers? The stronger demons have already beaten the lesser ones and have won the right to compete for Groom, it's archaic, but its our ways. It was how things were done in the early years to make sure that only the strongest demons mated with the few demonesses we had, and that only the strongest lineages continued."

"But Father-." Chloe frowned.

"Father could tell them that they can't force you-but these are laws put down by _him_." Lilith replied. "If Sam here wants to be eligible for Groomship again, he has to stop fucking around and get into the competition."

"Who says he wants to be Groom again? Who says I want him to be Groom again?" Chloe was pulling at straws, confused and a little intimidated by the fact that there'd been some gladiator-like fights going on for her and she hadn't even _known_.

"You...haven't slept with anyone else since we-?" Sam's voice surprised her by its shock. "You haven't-not even with Dean? He-he's not your Groom?"

Lilith snorted. "You seriously thought that he was her Groom? _Seriously_?" She turned to Chloe, having been the only demon other than Manny to know the truth about how much the blonde's separation from Sam had hurt her. "Oh, you make him pay for that."

Chloe clenched her hands, feelings swirling, so confusing, before she erupted into shadows and disappeared, racing away.

Sam watched her go, face conflicted.

"You're an idiot, you know this, right?" Lilith shook her head at him, folding her small arms over her flat chest. "This is all your fault. If you'd done what you were supposed to do and just transitioned while the girl was living with you she wouldn't have had to leave."

"Had to leave?" Sam frowned, turning his attention on the tiny, pint-sized demoness. "She was forced?"

"By _you_." Lilith replied testily. "Demons can't live with humans after a certain amount of time, not without sucking their life out of them, and the banshee was already crying your death. Chloe had no choice, she _had_ to leave you."

Sam's eyes widened, shock ridiculous on his face. "Azazel never told me..."

"Of course he wouldn't, my older brother's a bastard." Lilith snorted. "Plus, he knew that this way you'd work harder to become the demon we all know you can be."

Sam suddenly looked down at her. "Azazel's your brother?"

"Yes." Lilith nodded. "Lucifer is my father, Azazel and Belial are my brothers, you're my nephew, and Chloe's my cousin. You'll find that when you're high up on the demonic hierarchy you're surrounded by family."

The brunet frowned, running a hand through his hair. "If you and Azazel are siblings and Lucifer if your father...so that means Lucifer is Dean's and my grandfather...in essence."

Lilith chuckled. "Oh, it gets more complicated than that, but I'll leave that for...Dean...to explain."

He shot the demon in the child's body a look, wondering why she seemed so amused. "Why are you telling me all of this anyway? Shouldn't you be helping Belial with Chloe?"

"Chloe doesn't _want_ Belial, not before she bonded with her demon or after. She doesn't want any of the demons here. When you were _human_ her demon wanted you, accepted you as a Groom. She as a succubus was unable to resist you, a human, because of the strong connection her demon made with your dormant one. Not only does that speak about the _power_ your demon has, but about the connection you two have." Lilith leaned against the light pole Sam had pushed Chloe against sometime before. "Before, in our days of glory, that would have been respected. The moment you began your transitioning the demons would have left her alone, but there isn't any honor anymore. Even now, she's an older demon and yet despite her mind fighting you her demon accepted, once again she was unable to not want you. That was enough for me to realize you're still her Groom, her demon never really broke off your engagement and now that it knows you're transitioning it will _never_ accept another Groom but you."

Sam's lips slowly curved in a smile.

"Oh, don't celebrate yet." Lilith rolled her eyes. "You still have a long road before you can get her back. You'll have to fight."

"I'm fine with that." Sam replied.

"Good." She brushed her hands together. "Now, finish transitioning...oh...and go talk to your brother. He'll explain everything I can't."

Sam made a face at her. "Why would Dean know things you don't?"

She just grinned at him before reaching down and picking up a pink Barbie backpack he hadn't noticed before, beginning to walk away, singing softly to herself. "You can run, you can run, tell my friend Willie Brown...that I got the crossroad blues this mornin', Lord, babe, I'm sinkin' down..."

Sam watched her until she vanished into the darkness, before running his hand over his hair, going over everything he'd learnt that night.

Chloe hadn't left him because she didn't love him.

She'd left him...because she _had_.

Sam's lips curled in a smile, before he erupted into shadows, searching for his brother and the answers Dean apparently had for him.

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